Darth Garfunkel's first Sith job was in the Coruscant Department of Redundancy Department, where he enjoyed success as a low-level bureaucrat until failing to acquire necessary additional information pertaining to a mysterious female individual, thus leaving him unable to complete the relevant records.

Disgraced, Lord Garfunkel was summarily fired. While waiting at the airbus station (with a ticket for his destination), he first met his future partner, Simon the Killer Ewok, who was homeward bound for Endor.

Garfunkel, now teamed with Simon, embarked upon the mass murdering rampage for which he earned the epithet "The Big Bright Mean Dismemberment Machine." Republic authorities devoted considerable resources to tracking them down, but all their teams came back to them in shades of decapitation.

The infamous "Massacre in Coruscant Central Park" took place during this era; Garfunkel helped Simon to kill as many Coruscanti as they could before authorities arrived, and in the plaza there he saw ten thousand people—maybe more—people screaming without their limbs, people bleeding through bisected chins. Meanwhile, the words of the Jedi were written on the Temple walls, and Garfunkel cursed them all. The massacre was Garfunkel's greatest achievement as a Sith, though Simon took most of the credit.

Years later, Garfunkel encountered a rift in the space-time continuum and was transported into the X-Men universe, where he wooed and married Jean Grey, much to the consternation of Professor Xavier, who interrupted the wedding and got his legs broken by Simon for his trouble.